(5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2,4,8(5H,10aH)-trione

Base Information

• Chemical Name: (5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2,4,8(5H,10aH)-trione
• CAS No.: 1392307-75-3
• Molecular Formula: C₂₆H₂₈O₆
• Molecular Weight: 436.505

Synonyms:

Chemical Property of (5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2,4,8(5H,10aH)-trione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2,4,8(5H,10aH)-trione

There total 33 articles about (5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2,4,8(5H,10aH)-trione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(S)-4-benzyl-3-((2S,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-enoyl)oxazolidin-2-one → (5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2,4,8(5H,10aH)-trione (1392307-75-3)

Guidance literature:

Multi-step reaction with 19 steps

1.1: sodium tetrahydroborate / tetrahydrofuran; water / 0 - 20 °C

2.1: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C

3.1: dichloromethane / 20 h

4.1: diisobutylaluminium hydride / diethyl ether; toluene / -40 °C / Inert atmosphere

5.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / Cooling with ice

6.2: 0.25 h

7.1: pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

8.1: triethylamine / dichloromethane / 1 h / 50 °C / Inert atmosphere

9.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 20 °C

9.2: 2 h

10.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / hexane; toluene / 0.5 h / -78 °C

10.2: -78 - 0 °C

10.3: 9 h / 60 °C

11.1: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) / isopropyl alcohol / 2.5 h / 70 °C / Inert atmosphere

12.1: sodium isopropylate / isopropyl alcohol / 2 h / UV-irradiation

13.1: [2,2]bipyridinyl; tert.-butyl lithium / tetrahydrofuran; pentane / 0.75 h / -78 °C / Inert atmosphere

13.2: 0.83 h / -78 - -40 °C / Inert atmosphere

13.3: -40 - -25 °C / Inert atmosphere

14.1: ozone / dichloromethane / 0.2 h / -78 °C

14.2: 5 h / 20 °C

14.3: 48 h

15.1: chromium dichloride / tetrahydrofuran / 0.42 h / 20 - 50 °C / Inert atmosphere

16.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C

17.1: chromium dichloride; nickel dichloride / N,N-dimethyl-formamide / 1.75 h / 20 - 45 °C / Inert atmosphere

18.1: hydrogenchloride; water / methanol / 96 h / 20 °C

19.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C

With pyrrolidine; chromium dichloride; hydrogenchloride; [2,2]bipyridinyl; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); carbon tetrabromide; water; tert.-butyl lithium; sodium isopropylate; diisobutylaluminium hydride; Dess-Martin periodane; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; pentane; 2.1: Dess-Martin oxidation / 3.1: Wittig reaction / 7.1: Tsuji-Trost cyclization / 15.1: Takai olefination / 17.1: Nozaki-Hiyama-Kishi reaction;

DOI:10.1002/anie.201108223

Reference yield:

(2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol (1392307-50-4) → (5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2,4,8(5H,10aH)-trione (1392307-75-3)

Guidance literature:

Multi-step reaction with 18 steps

1.1: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C

2.1: dichloromethane / 20 h

3.1: diisobutylaluminium hydride / diethyl ether; toluene / -40 °C / Inert atmosphere

4.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / Cooling with ice

5.2: 0.25 h

6.1: pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

7.1: triethylamine / dichloromethane / 1 h / 50 °C / Inert atmosphere

8.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 20 °C

8.2: 2 h

9.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / hexane; toluene / 0.5 h / -78 °C

9.2: -78 - 0 °C

9.3: 9 h / 60 °C

10.1: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) / isopropyl alcohol / 2.5 h / 70 °C / Inert atmosphere

11.1: sodium isopropylate / isopropyl alcohol / 2 h / UV-irradiation

12.1: [2,2]bipyridinyl; tert.-butyl lithium / tetrahydrofuran; pentane / 0.75 h / -78 °C / Inert atmosphere

12.2: 0.83 h / -78 - -40 °C / Inert atmosphere

12.3: -40 - -25 °C / Inert atmosphere

13.1: ozone / dichloromethane / 0.2 h / -78 °C

13.2: 5 h / 20 °C

13.3: 48 h

14.1: chromium dichloride / tetrahydrofuran / 0.42 h / 20 - 50 °C / Inert atmosphere

15.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C

16.1: chromium dichloride; nickel dichloride / N,N-dimethyl-formamide / 1.75 h / 20 - 45 °C / Inert atmosphere

17.1: hydrogenchloride; water / methanol / 96 h / 20 °C

18.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C

With pyrrolidine; chromium dichloride; hydrogenchloride; [2,2]bipyridinyl; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); carbon tetrabromide; water; tert.-butyl lithium; sodium isopropylate; diisobutylaluminium hydride; Dess-Martin periodane; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; pentane; 1.1: Dess-Martin oxidation / 2.1: Wittig reaction / 6.1: Tsuji-Trost cyclization / 14.1: Takai olefination / 16.1: Nozaki-Hiyama-Kishi reaction;

DOI:10.1002/anie.201108223

Reference yield:

(4R,5R,6R,(E))-ethyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dienoate (1392307-51-5) → (5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2,4,8(5H,10aH)-trione (1392307-75-3)

Guidance literature:

Multi-step reaction with 16 steps

1.1: diisobutylaluminium hydride / diethyl ether; toluene / -40 °C / Inert atmosphere

2.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / Cooling with ice

3.2: 0.25 h

4.1: pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

5.1: triethylamine / dichloromethane / 1 h / 50 °C / Inert atmosphere

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 20 °C

6.2: 2 h

7.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / hexane; toluene / 0.5 h / -78 °C

7.2: -78 - 0 °C

7.3: 9 h / 60 °C

8.1: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) / isopropyl alcohol / 2.5 h / 70 °C / Inert atmosphere

9.1: sodium isopropylate / isopropyl alcohol / 2 h / UV-irradiation

10.1: [2,2]bipyridinyl; tert.-butyl lithium / tetrahydrofuran; pentane / 0.75 h / -78 °C / Inert atmosphere

10.2: 0.83 h / -78 - -40 °C / Inert atmosphere

10.3: -40 - -25 °C / Inert atmosphere

11.1: ozone / dichloromethane / 0.2 h / -78 °C

11.2: 5 h / 20 °C

11.3: 48 h

12.1: chromium dichloride / tetrahydrofuran / 0.42 h / 20 - 50 °C / Inert atmosphere

13.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C

14.1: chromium dichloride; nickel dichloride / N,N-dimethyl-formamide / 1.75 h / 20 - 45 °C / Inert atmosphere

15.1: hydrogenchloride; water / methanol / 96 h / 20 °C

16.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C

With pyrrolidine; chromium dichloride; hydrogenchloride; [2,2]bipyridinyl; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); carbon tetrabromide; water; tert.-butyl lithium; sodium isopropylate; diisobutylaluminium hydride; Dess-Martin periodane; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; pentane; 4.1: Tsuji-Trost cyclization / 12.1: Takai olefination / 14.1: Nozaki-Hiyama-Kishi reaction;

DOI:10.1002/anie.201108223

upstream raw materials:

(2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanecarbaldehyde

(2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol

(4R,5R,6R,(E))-ethyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dienoate

(4R,5R,6R,(E))-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dien-1-ol

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 1392307-75-3 (5R,7S,(9E),10aR,11R,12R,13R,14aR)-11-(benzyloxy)-6,7,11,12,13,14-hexahydro-5,7,13-trimethyl-12,14a,3-(epoxymethino)-2H-1-benzoxacyclododecyn-2,4,8(5H,10aH)-trione

Send

Send

Metric Ton KG G Pound L ML

Send

Send